Gorris, Hans H. and Saleh, Sayed M. and Groegel, Dominik B. M. and Ernst, Steffen and Reiner, Knut and Mustroph, Heinz and Wolfbeis, Otto S. (2011) Long-Wavelength Absorbing and Fluorescent Chameleon Labels for Proteins, Peptides, and Amines. BIOCONJUGATE CHEMISTRY, 22 (7). pp. 1433-1437. ISSN 1043-1802,
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Long-wavelength absorbing labels that change their color and fluorescence upon conjugation to proteins and other biomolecules provide two critical advantages over the wealth of conventional amine-reactive labels. At first, the progress of the labeling reaction can be monitored continuously either visually or by spectrometry without prior purification. Then, the labeled biomolecule can be investigated with red or near-infrared light, which minimizes background interference in biological samples. These unique characteristics are met by a group of long-wavelength absorbing cyanine dyes carrying a reactive chloro substituent for nucleophilic substitution with primary amines, which is accompanied by a color change from green to blue. In addition to this so-called chameleon effect, the dyes display an increase in fluorescence during the labeling reaction. Despite their structural similarity, the reactivity of the dyes differs strongly. The fastest labeling kinetics is observed with dye S 0378 as its five-membered ring affords a stabilizing effect on the intermediate carbocation during an S(N)1-type of nucleophilic substitution. The reaction mechanism of the amine-reactive cyanine dyes provides a blueprint for the design of future long-wavelength absorbing chameleon dyes.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | BIOGENIC-AMINES; DYES; SOLVOLYSIS; GREEN; PROBE; RED; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Analytische Chemie, Chemo- und Biosensorik > Chemo- und Biosensorik (Prof. Antje J. Bäumner, formerly Prof. Wolfbeis) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 08 Jun 2020 10:34 |
| Last Modified: | 08 Jun 2020 10:34 |
| URI: | https://pred.uni-regensburg.de/id/eprint/20582 |
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